Diosbulbiside A

Details

• Internal ID: 7e6e9c50-8e67-4ef0-bb53-ffd64e410955
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-2-[(1R,2S,4S,5'S,6R,7S,8S,9S,12S,13R,16S)-5',8-dihydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2O)OC3CCC4(C5CCC6(C(C5CC=C4C3)CC7C6(C(C8(O7)CCC(CO8)(C)O)C)O)C)C)CO)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]([C@H](O[C@H]([C@@H]2O)O[C@H]3CC[C@@]4([C@H]5CC[C@]6([C@H]([C@@H]5CC=C4C3)C[C@H]7[C@@]6([C@@H]([C@]8(O7)CC[C@](CO8)(C)O)C)O)C)C)CO)O)O)O)O
• InChI: InChI=1S/C39H62O14/c1-18-27(41)29(43)30(44)33(49-18)52-32-28(42)25(16-40)51-34(31(32)45)50-21-8-10-36(4)20(14-21)6-7-22-23(36)9-11-37(5)24(22)15-26-39(37,47)19(2)38(53-26)13-12-35(3,46)17-48-38/h6,18-19,21-34,40-47H,7-17H2,1-5H3/t18-,19+,21-,22+,23-,24-,25+,26-,27-,28+,29+,30+,31+,32-,33-,34+,35-,36-,37-,38+,39+/m0/s1
• InChI Key: BSDDPSKDLBDRSZ-NVNZNZKRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₆₂O₁₄
• Molecular Weight: 754.90 g/mol
• Exact Mass: 754.41395665 g/mol
• Topological Polar Surface Area (TPSA): 217.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.62
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

• CHEMBL1076253

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7571	75.71%
Caco-2	-	0.8828	88.28%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7376	73.76%
OATP2B1 inhibitior	-	0.8691	86.91%
OATP1B1 inhibitior	+	0.8602	86.02%
OATP1B3 inhibitior	+	0.8994	89.94%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.6271	62.71%
P-glycoprotein inhibitior	+	0.7212	72.12%
P-glycoprotein substrate	+	0.6746	67.46%
CYP3A4 substrate	+	0.7364	73.64%
CYP2C9 substrate	-	0.7915	79.15%
CYP2D6 substrate	-	0.8348	83.48%
CYP3A4 inhibition	-	0.9268	92.68%
CYP2C9 inhibition	-	0.9182	91.82%
CYP2C19 inhibition	-	0.9234	92.34%
CYP2D6 inhibition	-	0.9343	93.43%
CYP1A2 inhibition	-	0.9102	91.02%
CYP2C8 inhibition	+	0.7826	78.26%
CYP inhibitory promiscuity	-	0.9302	93.02%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5116	51.16%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9197	91.97%
Skin irritation	+	0.4929	49.29%
Skin corrosion	-	0.9426	94.26%
Ames mutagenesis	-	0.8507	85.07%
Human Ether-a-go-go-Related Gene inhibition	+	0.6774	67.74%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.9250	92.50%
skin sensitisation	-	0.9214	92.14%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6988	69.88%
Acute Oral Toxicity (c)	I	0.5904	59.04%
Estrogen receptor binding	+	0.8055	80.55%
Androgen receptor binding	+	0.7606	76.06%
Thyroid receptor binding	-	0.5973	59.73%
Glucocorticoid receptor binding	-	0.4641	46.41%
Aromatase binding	+	0.6601	66.01%
PPAR gamma	+	0.7100	71.00%
Honey bee toxicity	-	0.6376	63.76%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9176	91.76%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.78%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.59%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	97.80%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.65%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	95.09%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.16%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.86%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.25%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.85%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.28%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.22%	89.00%
CHEMBL2581	P07339	Cathepsin D	87.37%	98.95%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.03%	91.03%
CHEMBL1914	P06276	Butyrylcholinesterase	84.92%	95.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	84.31%	89.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.24%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.32%	95.50%
CHEMBL2243	O00519	Anandamide amidohydrolase	83.23%	97.53%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.20%	97.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.82%	92.94%
CHEMBL1951	P21397	Monoamine oxidase A	81.09%	91.49%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.78%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.74%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.64%	93.04%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.06%	94.00%

Plants that contains it

• Dioscorea bulbifera

Cross-Links

• PubChem: 44606589
• LOTUS: LTS0130024
• wikiData: Q104945179